The New Bed

Mistress finally decided that she did indeed want the new bed. It will be delivered early next week.

Once it’s fully assembled, I’ll have to work on the larger under-bed drawer. It’s designed to be able to hold a moderate amount of clothing. It will need to be retrofitted to hold something else: me.

That’s a project that, thanks to my Y chromosome and my well outfitted workshop downstairs, shouldn’t be too challenging. Swap out the bottom for some 3/4″ plywood, reinforce all the corners with L-brackets, and install a generous quantity of low-profile wheels.

Mistress will also want some sort of way to lock it from the outside. Nothing fancy, since I won’t be able to reach it anyway. She’s also talked about some restraints in the drawer itself, but that’s probably an add-on for the future.

I’m actually fairly nervous about this. I do have some claustrophobia that kicks in sometimes. We haven’t really played that much with it. I’m a bit worried that I’ll have more trouble with that kind of panic now that I’ve fully transitioned from male to female. I’m just more emotionally volatile. One example is that I had to safeword on the severe bondage hood that I used to absolutely love to wear. It freaked me out.

The drawer itself is long enough to fit me (being about the length of the bed frame). There is also plenty of width — almost enough for two people. But the height is my biggest concern. Based on the dimensions, I think my nose will just barely rub as the drawer is opened and closed, unless I turn my head. Plus it will be dark.

Mistress talks fondly of “being able to just put me in the drawer for the night”. I hope I can live up to her expectations. This is really going to stretch me in some edgy ways.

She continues to talk to her close friend “Tom” about all sorts of intimate details of my surgery and my new genitals. She also mentions occasionally about the “openness in our relationship”, hinting strongly that we’d entertain the idea of having sex with others. And she’s talking seriously about us making a trip to see him early next year.

I’m still not healed well enough to get back to my spanking backlog. Mistress has given me some 200 swat penalties over the last month for transgressions. But I also was forgiven 150 last week for some substantial housework. I think my current outstanding total is 868. I’m trying hard to be a good girl!

Our relationship is back of firm ground. This gender transition has really stressed her out at times. But we are returning to some normality in our daily lives. And that makes a huge difference for her. I’m pretty sure now that our relationship will survive long-term, which utterly thrills me! When she and I are good, my universe is right and joyful. And right now, I’m so grateful to be living in that.

Back in the groove

Changing from male to female has really stressed our incredibly strong relationship. It had been quite a few months since we’ve had any real substantial sexual interaction, much less kinky play. And certainly I need a break since surgery to let my new lady parts heal.

But within the last day or so we’ve had some breakthroughs. One started out simple enough. Mistress found some plastic pants that were not yet put away from our trip to Pennsylvania (for my gender surgery). We have had a small assortment of adult-size plastic and rubberized “diaper covers” from AB play in years past.

I had to wear adult diapers for several days after surgery, and these covers seemed sensible to bring. We ended up not using them. But this day she picked out the frilly lacy set with pink bows, and instructed me to wear them the rest of the day.

It might not sound like much, but it allowed her to humiliate me for hours. The crinkling of the plastic as I walked was noticeable. And she delighted even more when we went on a few errands. The light sweatpants did little to hide the sounds or the extra bulk of the plastic pants.

You might not understand how humiliation can be erotic – but for some of us it definitely is. And Mistress knows just how to push my buttons. Even though most my new genitalia are still numb from surgery, I can still feel aroused. Both at home and in public, her comments and smirks to me were very triggering that way.

This might not sound “normal” to you, but for our relationship it was a refreshing return to normality. And it seems to have made a big difference in her outlook for the future of our relationship. Having kinky play absent from our lives for so long was worrying both of us.

I’m also healed enough to be able to do things for her now (like leg massages, tasks around the house, etc). Those help reinforce her role as Dominant and my role as submissive. That had been upended recently as she cared for me for several weeks after my surgery.

She still talks a lot of needing more “male energy”, which is more than just a euphemism for “sex with men”. But I still expect that we’ll have both in our future. The topic of three-ways has been discussed, at her initiation, quite a few times.

She’s also talked more to her close friend Tom about my sex change, as well as hinted at some “openness” in our relationship. Tom’s a smart guy, but he hasn’t played any cards yet (that I know of) to follow her lead. It seems like it just might be a matter of time.

We are also still seriously discussing a new bed.


This trundle bed has a large drawer underneath on one side. Without a mattress, the drawer is just big enough for me to fit into. Mistress loves the idea of putting me in that drawer for the night sometimes. She’s also talked about restraints in the drawer, a lock on the outside, and the possibility of her having sex with someone else on the bed right above me as I’m locked in the drawer.

Long-time readers of my blog know that cuckolding has been a fascination of mine for decades. Combining it with bondage like this is really erotic for both of us. Stay tuned for more news!

Lesbian cuckold?

I’ve been living full-time as a woman for almost 14 months now, and I’ve been on feminizing hormones for even longer. One thing that means is that I can’t have penetrative sex anymore. To be blunt, my cock just won’t get hard enough for me to screw someone. Like my wife.

She loves to use this to humiliate me. This hormonally-induced impotence gives her lots of fodder for teasing. She doesn’t miss any opportunity to riff on words like limp, shriveled, tiny, ineffective, useless, etc.

She will also talk about being with other men for sex. I always – and I mean always – blush when she does. It’s involuntary. She’s even made be blush like that in front of friends, and they all find it humorous. Early on it seemed like she would talk about it just to tease. I’m not so sure anymore.

Yesterday our conversation turned to sex, and she asked me if I would like it if she were to have sex with a guy. I reluctantly said that I would understand, and that I wouldn’t mind. I said I sincerely wanted her to be happy. She asked me very specifically if that was my “final answer”. I said yes.

Tonight she told me she misses “man-sex”. I apologized for not being able to provide that for her any more. She said it didn’t matter, because she can get that whenever she wants, “Right?” I had to agree. After all, I honestly do want her to be fully sexually satisfied.

I know I can still satiate her sometimes. She lets me eat her out when she wants it. I never disappoint. But she says it’s not the same as a warm, firm penis inside her. I can’t dispute that.

I’ll be picking a surgeon this week for my Gender Conforming Surgery (which will convert my genitals from male to female). I think the finality of this is part of the energy that is going on.

I still can’t tell for sure if this “lesbian cuckolding” is something that she will go through with. More and more I am thinking that she will eventually. What’s unclear to me is whether she will get hers before or after she arranges for a man to take my newfound virginity. And I have no doubt at all that she will arrange that, if she hasn’t already.


Paving the way?

I’ll probably appear to be a bit fixated on this topic, but I wanted to share a conversation from last night while it’s still fresh in my mind.

My wife revisited the “jealousy” topic (see my prior post) after we went to bed. She wanted to talk about it more, in some detail. It surprised me.

She started out saying she wanted to be sure she understood how I thought I would feel if she were to have sex with another guy.  “So, you’re telling me you wouldn’t be jealous?” she asked.

“Well, like I said before, if it threatened our relationship, like if you wanted him instead of me as a life partner, then yes, I think it would be terribly hurtful for me. Not in a erotic humiliation sort of way, but in a severe depression and life sucks sort of way.” I continued, “But if it was just sex and not a deeper, emotional relationship, then… I don’t think I’d be jealous.”

She still seemed surprised. “I just don’t get that,” she said.

I asked her “Well, how would you feel if I had an affair?” Her response was immediate and firm. “Oh, that’s easy. I’d leave you immediately and we would get a divorce as soon as possible. I hope that’s clear. Is it?” I said “Yes, Ma’am, very clear. That will never happen.”

There is no doubt that this is a female-led relationship, that she is the dominant, and that I am her submissive.

“Let’s walk through a scenario,” she said. “You imagine it happening for real, and tell me how you feel.”

She continued. “You come home from work someday, and things look a bit messier than usual in the house, like maybe I’ve been distracted most of the day. You don’t find me downstairs, but hear something upstairs and come into our bedroom. There you see me naked on the bed with another man. We’re having sex, and the room smells like we’ve been doing it for hours. I don’t hear you, as I’m just about to orgasm again, and I do, making quite a bit of noise. Then I do notice you, and tell you to shut up and sit down. What do you do?”.

I said “I’d quietly sit down, without saying ‘Yes, Ma’am, right away’ as you’ve instructed, because you said to shut up.” She replied “Very good. And how would you feel?”

I pondered this, trying to put myself into this mythical situation. It was difficult to separate the idea of this really happening from a fantasy (one I’ve had many times). I answered her, “Well, I would feel surprised, shocked, and maybe a little hurt. But I’d also feel somewhat good that you were enjoying yourself so much, being sexually satisfied by him.”

Then she asked “How about if he was giving me oral sex? How would you feel about that?” That answer seemed easier: “I’d feel a little more hurt by that, since I really enjoy going down on you, and it’s something I can still do.” She didn’t miss the opportunity to rub it in, saying “Yes, I guess that is the one way you can still satisfy me sexually. We both know that, thanks to the hormones, tiny is more worthless than ever.”

She put her hand down my pajamas to check tiny’s status and said “This is turning you on, isn’t it?” I had to admit that it was (it always does). The answer to her question was obvious, but despite that, we both knew that there wasn’t enough there for me to sexually satisfy her. My size, thickness, and firmness has substantially decreased; a year of feminizing hormones will do that.

She rolled over onto her stomach, and put a hand down between her legs. She made a point of telling me “I’m going to masturbate now, thinking about having sex with a black guy I met at a swingers party before I met you. He had a magnificent cock. I gave him a bj back then. I might still have his email address. It might be time to reconnect. Mmmmm.” She started moaning and bucking her hips. I put my hand on her thigh to feel her gyrate until she came, relaxed, and got quiet.

It feels like I’ve just gone past that point — where those who want to be cuckolded suddenly realize that this might not be just a fantasy anymore, and that it’s truly out of their control. Maybe she’s just mindfucking me again. But what if she isn’t?

And yes, it really did happen like this last night.


My wife asked me today if I have ever been jealous, not just with her, but at all with anyone. I had to stop and think. And even then, I wasn’t sure.

My trust in her is so high, and we have such a strong relationship built on honesty and communication, that it’s truly never come up for me. Fidelity (or even flirting) in my previous marriage wasn’t an issue either.

So I find myself with about 30 years of married life and no real opportunities for me to feel jealous. Is that weird?

I also realized that my wife has never expressed significant interest in someone other than me. So it’s probably fair to say that we’ve never “gone there”.

The astute reader of my blog will recall that I’ve shared many stories here that my wife has told me about black men that she’s had sex with. They are great stories, and I see myself as a cuckold candidate because those stories turn me on. But they have always only been stories that she uses to humiliate me.  After all, what kind of husband gets turned on hearing about his wife being unfaithful?

She took her questioning on the topic further, by asking flat out: “Do you think you’d feel jealous if I really did fuck another guy?” Again, I think it was weird that I had to think about my answer so much.

Eventually my answer was: “Well, if our relationship was threatened by it, then yes, I probably would feel jealous. But if it was just sex, well, probably not. It might also depend on whether or not I was present — but I’m not sure on that part.”

Many people have a strong connection between emotional intimacy and sexual intimacy. I’m like that in my primary relationship: if we’re emotionally struggling, I’m just not going to feel like having sex.

But my wife is not like that. She and a former husband, when they were married years ago, used to go to swingers parties. And yes, participate. But their relationship didn’t have the depth ours does. Swinging has not been a part of our time together.

My wife took it further.  “So, if you came home one day and I told you I invited our friend Donny over, and rode his magnificent cock to several orgasms while you were at work, you wouldn’t be jealous?” Since I know that Donny doesn’t threaten our relationship at all, my only honest answer was “Well, no, I don’t think it would.”

“Hmmm….” she said teasingly, as she walked off towards her office (and her computer).

So my question for you is:  now that I’m a female in a married lesbian relationship, could I still be considered a cuckold?



Mistress and I entertained her sister today. It was the first time I was dressed in my female role in front of a family member. It went very well.

We were eating a late lunch out on our deck, and the two of them were talking about men and relationships. Somehow the conversation turned to black men, and Mistress made me quite embarrassed. She told her sister about the man adjacent to her workplace, how attractive he is and what a nice sexual partner he would make. He’s the one she teases me about having sex with a lot (I’ve blogged about that many times before).

Her sister thought she was just lightly teasing me, so Mistress went further. She said “just because my spouse won’t be able to please me like a man, that doesn’t mean I won’t get any.” Her sister laughed like it was a joke, and Mistress just sat there with a smile. I blushed like I had too much makeup on. “After all,” Mistress clarified, “I’m not a lesbian, I’m bisexual.”

At another point in the conversation Mistress told her sister “Chastity isn’t so bad,” when talking about her sister not dating for a while. Of course that was a subtle dig at my locked up cock.

After her sister left, we stayed on the deck to chat. I found an inchworm and we watched it for a while. Mistress named it “tiny”, for obvious reasons. “Go, tiny, go!” she said as it slowly moved across the table. At one point I remarked that he was “straight up”, and her quick reply was “Well, I haven’t seen anything like that in quite some time.” I observed that it was by her choice, and she just smiled.

Mistress used me for her own orgasm this morning. I really enjoy being used like an object that she uses for her own pleasure. I mentioned to her that it turned me on. She said she didn’t notice, and that it doesn’t matter anyway. I love it that she’s right — that her sexual pleasure matters and mine doesn’t.

Now with more security

Mistress went to visit some relatives late last week. She took the emergency keys to our biometric safe with her. The keys to my chastity cage are in that safe, which opens only by her fingerprint. The safe is cabled securely in our closet.

Until now she had “hidden” those emergency keys in our house. She teased me at times to try to find them, but I dared not look as I didn’t wanted to be tempted to let myself out of chastity. The corporal punishment consequences for that would not be good, and I couldn’t live with the guilt. So it’s actually good that those keys are gone and locked in her relative’s gun safe over an hour away.

We still have a spare set of chastity keys in a tamper-proof box. But the security of my chastity significantly increased by her decision to relocate the keys to our safe.

Before she left she teased me pretty significantly. She reminded me about how why I was locked up: because tiny (her name for my cock) is so small and inadequate for her needs. She said she might find another guy to have sex with while she was away. Some stud with a man-sized cock that could really please her. And she asked me what I thought about that. I said “I want you to be happy, even if that’s what it takes” and I meant it.

In the end she was too busy with the relatives to do anything else — or so she tells me. I expect that’s true, since her finally cuckolding me for real would be a new level of humiliation that I’m quite sure she would want me to experience.

I’m continuing to come out to more friends about my plans to transition into a woman. Mistress is supportive, in fact we told her sister today. I’m hoping to start hormones this month, and am continuing to work with professionals on moving forward. Some days I’m scared about how fast things are moving, other days I’m frustrated that we’re not further along in this (roughly) 2 year process.

Mistress and I went out to a pretty busy restaurant this weekend, and I was dressed up pretty. She went with a rather butch look (jeans, jean vest) while I had on a nice dress with hose and matching low wedge shoes. I seemed to completely pass as a woman, which is great.

Lately I’ve had an issue with the chastity cage when crossdressing. Since the cage is bulky I have to really tuck it between my legs. Twice now one testicle has slipped through and escaped between the base ring and the base of the cage. That’s my own fault, of course, for ordering a base ring 2 sizes larger than I wore on my CB-3000 (which I’ve previously blogged about at length).

The last time it happened I requested the keys to get that testicle back into place. This time I worked pretty hard to push that naughty ball back through that narrow space. Nasty! I think I bruised it. Weird how I can not even notice it slipping out. Yet getting it back through is torture. Ah, what we go through to look beautiful!

For those curious about transsexuality, I’ll again recommend the book She’s Not There – A Life in Two Genders. I finished it, and it was very, very good. Hard for me to read in spots, as it got so personal. But very education, very readable, real, and well written.


Saturday morning I awoke to my wife pulling my hand between her naked thighs. She does this when she wants to use the palm of my hand to bring herself to an orgasm. I think she said something like “You know what to do, get busy”; I was groggy. I applied the pressure to her crotch the way she likes it, and she started grinding against my hand and stimulating herself.

When she reached under my pink, frilly nightshirt towards my nipples, I expected some teasing. She loves to stimulate my sensitive nipples, which makes tiny (her name for my cock) get hard, and drives me crazy with sexual wanting that she will then ignore (because that turns her on too).

Instead she started kneading my breast with her hand. As her breathing got heavier and faster she whispered in my ear: “I’m pretending that you have real breasts.” Wow. Our recent discussions about my gender issues is fueling her fantasies, which I thought was pretty cool. I laid there and let her grope me and use me for her pleasure. It was really wonderful.

Soon she had an orgasm, and relaxed. I laid there patiently and lovingly, my arm still trapped between her legs, her hand still resting on my chest. I was aroused, as I almost always am when she uses me to achieve her own sexual pleasure. But she ignored my state and enjoyed her post-orgasmic sensations. I became aware of how fulfilled I felt, having simply been an object for her sexual satisfaction.

Eventually she suggested that I get out of bed and start my chores. Saturdays I wear my basic housekeeping dress (as opposed to my formal service one). My chores including sweeping and then hand-scrubbing the kitchen and downstairs bathroom floor, vacuuming the stairs and landing and master bedroom, sweeping the upstairs bathroom, and cleaning the cat boxes. There are usually dishes to take care of too.

The biometric safe she ordered has arrived. She didn’t leave it unattended for a moment from when we took it out of the box until it was programmed to only open using her fingerprints. The keys to my chastity device are locked into it. The safe came with “emergency” keys to open it without fingertip scanning. But she told me today that her son has agreed to lock those keys into his own safe. He lives 1.5 hours away.

She made clear to him that “he is to give those keys only to her – ever”. He’ll be stopping by tomorrow, and she plans to give him the keys then. I’m pretty sure he’s quite curious about just what she is locking up that she doesn’t want me to access.

Biometric safe

Biometric safe

I can certainly recommend this type of safe to spouse/keyholders. It allows the keys to be totally secure and also handy. We got ours for $99 (including shipping) on eBay.

My wife’s one concern was that I would be able to surreptitiously slide her finger across it while she was asleep. Fortunately the box beeps loudly when it is used. Once when it is turned on, once when a scan succeeds, and twice if a scan fails. Her tests show that several tries are usually needed to open it, resulting in lots of beeping — and that’s when she’s being careful about it. Besides the risk of being caught, the likelihood of even succeeding at that would be really low. I know I wouldn’t even attempt it.

However, she’s still interested in securing the safe somewhere. It comes with a security cable allowing it to be locked to something. One idea I had was to run the cable through the wall between the attic and our master bedroom, and around a stud. This would literally cable the box to the house, well away from the bed. Yet it would still be handy enough to use, if/when she wanted.

Because it often seems to take multiple tries before her finger scans succeed, it gave me an idea about a chastity release game. On certain occasions Mistress would try some number of times (once? 3 times?) to scan her finger and open the safe. If it worked – lucky slave, time to get unlocked. If not – oh, too bad, maybe next time.

My wife’s sister was in town this weekend. We couldn’t trust her with any of our kinky stuff (unlike all the chastity fantasy stories), so my wife wouldn’t tell her about my crossdressing or chastity. However, my wife did make a comment to her, right in front of me, about enjoying multiple men and how I don’t mind. They laughed about it, and I blushed and said nothing.

Tuesday afternoon I have my first gender counseling appointment. I expect it will be somewhat non-eventful, involving some general background, paperwork, and preparation for taking some tests. I’m still a bit anxious about this Pandora’s box.

My last dose of antibiotics will be Wednesday morning. She has said that I’m going back into chastity as soon as I’m done taking that medication. She’s being extra careful due to her concern that the chastity cage might have played a role in how the infection started. The most likely explanation we’ve been given is “ingrown hair follicle that became infected”. The cage can just manage to touch the wound site if I am laying on my stomach. Regardless, Mistress gets to decide.

I honestly can’t wait to be locked back up. I just don’t want to even be tempted. I want that secure feeling again. And I want to get back to being denied and teased and humiliated. I am craving my role as her chaste pet.

ObLink: I liked this story on Altar Boy’s site. It claims to be true, which I can believe. I like how the wife leverages her control and enjoys deepening his humiliation. I particularly like what she makes him do after she allows him to have intercourse with her (and his description of what that is like for him). Not all keyholders would be this intense, but I’m happy for them both (and a bit jealous of his situation).


I am expecting my wife and keyholder to decide to return me into chastity full-time sometime over the next week. My serious skin infection is healing nicely, but being on two antibiotics has really sucked.

I’m looking forward to putting the cage back on. I haven’t even tried it out since the resizing, and I feel sad about that. The new base ring dimensions will, we hope, solve the arousal/pain problem, allowing for long-term use with no need for removal.

I posted previously about discussions that my wife and I have had about my body, genitals, and gender. She teases me sometimes about having me castrated – which apparently is a very quick and relatively simple procedure when performed by someone qualified. She recently reminded me that I’m the one that brought it up early in our relationship, something I sincerely don’t recall discussing with her. But I suppose I did. She’s even teased about turning me into a full eunuch (no genitals at all).

More substantially, though, we’ve been talking about my gender role and identity. As I’ve been able to spend many more hours per week crossdressed at home (and sometimes carefully in public), things feel different. My wife commented how happy and content I seem to be when I am in my female role.

While at face value the comment didn’t surprise me, we talked further and I realized that she had a substantial point. I feel better, more complete, whole, myself, feminine, comfortable, at ease, happier, and so on when I am presenting as a woman. We both realized this could be something deeper.

Since that conversation we’ve talked a lot more, and I’ve observed myself and my emotions more closely. I was surprised about several things. I realized I do feel somewhat resentful of having to wear my “boy clothes” to work and elsewhere in public. It occurred to me that I have disliked my body hair for decades. Now that I’ve grown out my hair, I love brushing it, and I (surprisingly) don’t resent the extra effort.

We both took the BSRI (BEM Sex Role Inventory) test on-line (you can too – please add a comment about your results). My wife scored +18, I scored +11. Most men would score below zero (e.g. -20). Now since this test was developed in the 1970s, some professionals suggest it needs to be recalibrated for societal shifts since then. Still, it’s a well known professional tool.

Another wonderful aspect of all this is that my wife is completely supportive of this journey of discovery for me. She’s helped me find some gender identity counseling resources in our area. I have my first appointment next week. And she’s made clear that she is committed to me regardless of what genitals I may (or may not) have.

Since she is bisexual and tends to find women more attractive than men in general, there’s an interesting relationship dynamic there too. She said “It would be wonderful if you could get on hormones and grow some real breasts”. She is also happy to consider us living in public as two lesbians, if that’s where things end up.

Is this just some sex-change fantasy thing? It feels like more than that (to both of us). Until recently, when I have had the safety of this relationship and her unwavering love and support, I haven’t been able to even think such thoughts. It simply wasn’t an option to even consider, so there was no sense in seeing it as any more than a fantasy. But now, my sense of self and identity feels called into question, in a sincere and somewhat frightening way.

I shared with my wife a thought experiment I came up with. Consider this: You are offered all necessary gender alteration surgeries for free with no side effects or risks – would you do it? My wife’s answer for herself is a strong no. My gut-level instinctive answer is yes, but I feel myself block that answer with all sorts of fear and rationalizations and junk.

Miguel Ruiz, in his book The Four Agreements, beautifully clarifies the role of society as responsible for “domesticating the human”. I have been domesticated as a male. But is that who I am inside? How do I integrate these seriously feminine aspects of who I am without damaging my existing relationships (e.g. family, work, etc)? I easily feel overwhelmed about this lately.

I also realized that, as long as I can orgasm, which genitals I have doesn’t matter to me that much. My wife pointed out that my strong desires for chastity and useless penis humiliation could indicate a psychological dissatisfaction with my male genitals. That blew me away.

Am I just getting off on this as a fantasy? No, these discussions don’t turn me on, if anything they illuminate the fact that I’ve fallen into a rabbit hole, destination unknown. I’m experiencing a lot of confusion, many strong emotions, some loss of that sense that I know who and what I am, and some fear that I don’t know where this will lead. I’m open to all possibilities, including remaining just as I am after some counseling to get my head straight.

Oh, and my wife made it clear that we definitely would be getting a female chastity belt for me, if I end up as a woman. She wisely knows that the sexual servant/slut part of me would have an extremely difficult time being chaste. She also clarified that she would have no interest in a dildo attachment for my belt (to fuck her), as that’s what her other (likely black) male lovers would be for. But she certainly would look forward to strapping one on herself and fucking me in all of my holes.

Since this blog is primarily intended to be about my experience in chastity, I promise to return my focus to that – as soon as I am locked back up. This is only the beginning of my gender identity journey. And likely the beginning of some long-term chastity too, very soon.

P.S. In case it needs explaining, the title of this post is a tweak to the word “ambidextrous”, whose first dictionary definition is “using both hands with equal ease”. As I explore androgyny and my feminine side, it seemed to relate.

Permission to Enter

“Make your tiny cock hard, and rub it against my clit. I want an orgasm,” my wife and Mistress said.

This would be as close as I’ve been to being inside her for over two months. The prospect of feeling her warm, soft pussy lips against my unlocked cock was going to be quite a treat for me. Just imagining how the moistness of her labia would feel against the head of my cock made me quickly get hard for her.

I guess being out of my chastity cage for a week (while it gets resized) has more benefits than I realized.

She pulled the bed covers down, revealing her unclothed bottom half. Slowly she bent her knees and separated them, revealing her genitals to me so seductively. As I moved into position, she pulled her glistening pussy lips apart, revealing her sensitive nub that apparently needed some attention.

I lowered myself and gently put my cock head against her opening. She startled – apparently my PA ring was cold. Damn. “I don’t want that ring there; slide up further,” she directed. I did so, and my cock head approached her belly button. My shaft pressed against her clit now, and she started enjoying the pressure.

She began to grind herself against me, and I realized that this position gave me basically no glans stimulation at all. So I redirected my attention to ensuring that her pleasure was uninterrupted. It didn’t take her long to climax, after which I snuggled in and just hugged her as she floated in that post-orgasmic state.

Eventually she opened her eyes, smiled, and asked “I suppose you’d like to go inside me?”. I responded “Of course,” fully expecting her to decline as part of her ongoing teasing. She said “Well, it’s probably going to be a hassle to remove that ring, you probably need some tool from downstairs…” She likes to leverage any excuse to deny me.

“Actually, Mistress, the tool happens to be right here on the dresser,” I said. I could tell by her smirk that she was amused that I had anticipated this possibility. Even so, I expected only to be taunted further. Just because I’m unlocked from chastity for a few days doesn’t mean she would allow me to have intercourse with her. I briefly fantasized about being allowed to just rub my cock head against her now very wet pussy lips for a minute or two, and then she’d roll over and go to sleep.

Which is why I was shocked when she said “Ok, take it [the ring] out.” I quickly removed the 8 gauge ring from my pierced cock and rejoined her on the bed. Just to be sure, I asked: “Mistress, please may I cum inside you?” I couldn’t believe it when she agreed. Despite his lack of use, tiny (her name for my cock) remained hard enough for me to slip inside her wonderful, warm, wet, snug, delicious pussy.

It had been well over two months since she had last permitted this. As a result, the intensity of the sensation was very high, and it didn’t take me long at all to orgasm. It’s good that she had hers first, because I I don’t think I could have lasted long enough to bring her over the edge. It was so incredible to feel her vagina hugging tiny again. I felt extremely grateful to have been allowed that pleasure.

As we chatted afterwards, I got the impression that she was going to want more intercourse going forward. She wanted that pleasure for herself. I’m not sure how that’s going to work when, probably early next week, I’ll be locked back into chastity. Taking my captive bead PA ring out is super easy. Removing the PA lock and the JailBird is nowhere near as quick. But I guess that’s my problem, not hers, right?

Of course I’m also assuming that she meant more intercourse with me. Although she teases me a lot and talks about sex with other men often, I don’t think she’s serious about actually doing it. Sometimes I think I must be crazy to want that and to be locked up for months myself, instead of having sex with her myself.

Having experienced a little serious chastity and denial, I find myself drawn deeper into it. During these days of being unlocked, I find myself a bit uncomfortable about having free access to my cock. I’ve even urinated standing up a few times, and it feels like I’m getting away with something. It’s as if something in me has switched over to chastity as the norm for me now.

In related news, I completed a modification to the PA lock. There was a part of the brass locking cylinder that stuck out. The corners of that little metal piece would poke into my scrotum providing wincing-level bad pain on occasion. It turned out to be quite easy to file down that piece and round the remaining edges. It doesn’t diminish the lock security in any way, and it should be much more comfortable.

I actually am really looking forward to getting locked back into my resized JailBird. I sent it back to have the base ring enlarged. The problem was that when Mistress would get me seriously aroused, that base ring would get so tight I could barely stand it. Because the PA-lock prevents pull-out, a larger base ring isn’t a security concern.

I expect that the new base ring and increased lock comfort will allow me to wear the JailBird continuously for weeks or months. Whatever Mistress wants.

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